Dimethylformamide → Boc-Gln-Gln-Gly-OMe

HRID 246914Notes

Reaction equation

HRID 246914 reaction equation
[NH:1]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:2]([C:8]([O:10]C1C=CC([N+]([O-])=O)=CC=1)=O)[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].O[C:28]1[C:36]2[N:35]=N[NH:33][C:32]=2C=C[CH:29]=1.C(N1CC[O:42]CC1)C.[C:45]([O:48][CH2:49]C)(=[O:47])[CH3:46].C[N:52]([CH:54]=[O:55])C>>[NH:1]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C@H:2]([C:8]([NH:35][C@H:36]([C:32]([NH:33][CH2:46][C:45]([O:48][CH3:49])=[O:47])=[O:42])[CH2:28][CH2:29][C:54](=[O:55])[NH2:52])=[O:10])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7525EthylmorpholineHCID 8857Ethyl AcetateHCID 7017891L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl esterHCID 178418300HCID 178418300, compound

Product 1

HCID 131714598Boc-Gln-Gln-Gly-OMeYield 82%

Procedure

A solution of the residue obtained in the preceding step (theoretically 175.9 mM) in 500 ml of DMF, cooled on an ice bath, has 77.6 g of Boc-Gln-ONp (211.1 mM), 26.4 g of hydroxy benzotriazole (211.1 mM) and N-ethylmorpholine added thereto until a pH of 7 is obtained. After 20 hrs. of reaction at ambient temperature, the solution sets en masse. By addition of ethyl acetate, a precipitate is obtained which is drained, washed with AcOEt and dried in vacuo. 64.27 g of product are obtained, viz. a yield of 82%. Monitored by NMR and TLC.

Workup

  1. temperaturecooled on an ice bath
  2. additionadded
  3. customuntil a pH of 7 is obtained
  4. customof reaction at ambient temperature
  5. customa precipitate is obtained which
  6. washwashed with AcOEt
  7. customdried in vacuo

Sources & evidence

ORD record
ord-839e1ab7a8194256b1fb8d7c2497aa41
Source dataset
uspto-grants-1987_11
Patent number
US04704450

Reaction notes

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